Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

The diastereoselective synthesis of (−)-denticulatin A ( 1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spann...

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Bibliographic Details
Published inTetrahedron Vol. 53; no. 27; pp. 9169 - 9202
Main Authors De Brabander, Jef, Oppolzer, Wolfgang
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 07.07.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SECONDARY ALCOHOLS
KETONES
ENANTIOMERICALLY PURE
ASYMMETRIC-SYNTHESIS
POLYPROPIONATE METABOLITES
PULMONATE SIPHONARIA-DENTICULATA
ANTI-ALDOLS
CRYSTALLINE
ALDOL BOND CONSTRUCTIONS
STEREOSELECTIVE SYNTHESIS
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Summary:The diastereoselective synthesis of (−)-denticulatin A ( 1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C 4–C 8 in key intermediate 8. In addition, denticulatin B ( 1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00617-0